40983-58-2Relevant academic research and scientific papers
Gram-scale carbasugar synthesis: Via intramolecular seleno -Michael/aldol reaction
Banachowicz, Piotr,Buda, Szymon
, p. 12928 - 12935 (2019)
Carbasugars represent an important category of natural products possessing a broad spectrum of biological activities. Lots of effort has been done to develop gram scale synthesis. We are presenting a new approach to gram scale synthesis of the carbasugar skeleton via intramolecular seleno-Michael/aldol reaction. The proposed strategy gave gram amounts of 6-hydroxy shikimic ester in a tandem process in 36% overall yield starting from d-lyxose. We have attempted to demonstrate the synthetic utility of 6-hydroxyshikimic acid derivatives by covering the important synthetic modifications and related applications, namely synthesis of protected (-)-gabosine E, (-)-MK7606, (-)-valienamine and finally unprotected methyl (-)-shikimate.
Sequential C-C, C-O, and C-N bond-forming reaction of methyl (-)-3-dehydroshikimate, malononitrile, and bromoalkanes: Simple synthesis of 2-(alkylamino)-3-cyanobenzofurans from a biomass-derived substrate
Wang, Dejian,Zhang, Ensheng,Xu, Tianlong,Sheng, Jianfei,Zou, Yong
, p. 287 - 293 (2016)
An interesting and simple method was developed for the synthesis of 2-(alkylamino)-3-cyanobenzofurans by consecutive C-C, C-O, and C-N coupling reaction of methyl (-)-3-dehydroshikimate with malononitrile and a bromoalkane or dibromoalkane under microwave
Deoxy-nitrosugars. Synthesis of Methyl Shikimate and of Diethyl Phosphashikimate from D-Ribose
Mirza, Sohail,Vasella, Andrea
, p. 1562 - 1567 (1984)
The chain elongation of the deoxy-nitroribose 6 by a Michael addition to the vinylphosphonate 7 followed by a solvolysis gave the heptulosephosphonate 11 (87percent).From 11, the key intermediates 15 and 16 (77percent) were obtained by a highly diastereos
Synthesis of (-)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one
Oritani, Takayuki,Ueda, Rumi,Kiyota, Hiromasa
, p. 2106 - 2109 (2001)
The synthesis of methyl (-)-shikimate [(-)-2] was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis
Synthesis of (6S)-6-fluoroshikimic acid
Song, Chuanjun,Jiang, Shende,Singh, Gurdial
, p. 2833 - 2838 (2003)
(6S)-6-Fluoroshikimic acid 2 and (6R)-6-hydroxyshikimic acid 16 have been synthesised via an OsO4-catalysed dihydroxylation of diene 8, which was derived from (-)-shikimic acid 1.
Biomass-involved synthesis of: N -substituted benzofuro[2,3- d] pyrimidine-4-amines and biological evaluation as novel EGFR tyrosine kinase inhibitors
Sheng, Jianfei,Liu, Zhihong,Yan, Ming,Zhang, Xuejing,Wang, Dejian,Xu, Jun,Zhang, Ensheng,Zou, Yong
, p. 4971 - 4977 (2017)
Shikimic acid (1) is a renewable biomass which could be obtained sustainably through natural product isolation or metabolic engineering. Owing to its great potential in chemical conversion, the value-added utilization of this non-grain biomass has received much attention in recent years. Based on the established transformation route from shikimic acid (1) to methyl 3-dehydroshikimate (3-MDHS, 2) and to the multi-functionalized methyl 2-amino-3-cyanobenzofuran-5-carboxylate (3), we disclose a facile and transition metal-free method to access a series of N-substituted benzofuro[2,3-d]pyrimidine-4-amines in 63%-90% yields. The identification of these compounds as EGFR tyrosine kinase inhibitors has also been described. Among them, compound 5h exhibited the most potent inhibitory effect against EGFR tyrosine kinase with an IC50 of 1.7 nM and excellent antiproliferative activity against A431 and A549 cell lines with a GI50 of 5.1 and 12.3 μM, respectively.
An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach to Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray
Du, Lin,Munteanu, Charissa,King, Jarrod B.,Frantz, Doug E.,Cichewicz, Robert H.
supporting information, p. 1989 - 1999 (2019/08/20)
The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans a
Novel 4-benzamino-benzofuran[2,3-d]pyridine compound and application thereof
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Paragraph 0049-0053, (2019/01/23)
The invention discloses a novel 4-benzamino-benzofuran[2,3-d]pyridine compound and application thereof. The 4-benzamino-benzofuran[2,3-d]pyridine compound as shown in a general formula (I) as well asa pharmaceutically acceptable salt, a hydrate, a solvate or a predrug with anti-tumor effect. The experiment proves that the 4-benzamino-benzofuran[2,3-d]pyridine compound has a good inhibition effecton human lung adenocarcinoma cells A549, human large cell lung cancer cells H460 and Gefitinib medicine-resistant human lung adenocarcinoma cell strains H1975 (containing high-expression T790M/L858 double-mutation EGFR) and can be used for preparing anti-tumor medicines. (The formula is as shown in the description).
Economical Process for Preparation of the 19-nor A Ring of Paricalcitol from (-)-Shikimic Acid
Zhou, Shengfeng,Zhu, Runyu,Hu, Jingwen,Zhang, Lixiong,Lu, Qian,Yu, Xinhong
, p. 1887 - 1891 (2019/08/26)
An economical and efficient means of preparing the 19-nor A ring, a key precursor of the vitamin D receptor (VDR) activator Paricalcitol, is here described. This process begins with commercially available (-)-shikimic acid and was easily scaled up to kilo
Preparation method of paricalcitol intermediate
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Paragraph 0047; 0048; 0049; 0050; 0088; 0089, (2018/01/11)
The invention discloses a preparation method of a paricalcitol intermediate, which includes the following steps: (1) shikimic acid is esterified; (2) hydroxyl groups at sites 3 and 5 are selectively protected; (3) hydroxyl group at site 4 is protected by
